Lithium hydroxide, monohydrate → 3-Cyano-4-methoxybenzoic acid

HRID 385133

Reaction equation

HRID 385133 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8]C)=[O:7])#[N:2].O.[OH-].[Li+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 2801011Methyl 3-cyano-4-methoxybenzoate

Product 1

HCID 219909723-Cyano-4-methoxybenzoic acidYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-4-methoxybenzoate (879 mg) was dissolved in tetrahydrofuran (8 mL) and water (4 mL), and lithium hydroxide monohydrate (772 mg) was added to the solution, and then the mixture was stirred at mom temperature for 1 hour. The organic solvent was distilled off under reduced pressure and acidified with 2N hydrochloric acid, and then the precipitated crystal was collected by filtration to obtain the title compound (754 mg) as a colorless crystal.

Workup

  1. distillationThe organic solvent was distilled off under reduced pressure
  2. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-afce05d383564db4869144b7ab6bb707
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Linked notes

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